potassium carbonate in N,N-dimethyl-formamide T=110 - 120°C; 5 h;

potassium carbonate in N,N-dimethyl-formamide T=45°C; 18 h;

in water; N,N-dimethyl-formamide

sodium hydroxide; dihydrogen peroxide T=25°C; 4 h;

copper(l) iodide in methanol; N,N-dimethyl-formamide 4 h; Heating;

copper(l) iodide; sodium 1.) 15 min, 2.) DMF, reflux, 4 h; Yield given. Multistep reaction;

1: 96 percent / K2CO3 / dimethylformamide / 5 h / 110 - 120 °C 2: 70 percent / KMnO4 / acetone; H2O / 3 h / 50 - 60 °C 3: 90.7 percent / SOCl2 / benzene / 1 h / Heating View Scheme

1.1: boron tribromide / dichloromethane / 2 h / 20 °C 2.1: sodium hydride / N,N-dimethyl-formamide / 3 - 5 °C / |Inert atmosphere 2.2: 13 h / 20 °C / |Inert atmosphere 3.1: ethanol / 0.67 h / |Reflux 4.1: sodium tetrahydroborate / N,N-dimethyl-formamide / 0.33 h / 20 °C 5.1: 2,2'-azo-bisisobutyronitrile; tri-n-butyl-tin hydride / toluene / 2 h / |Inert atmosphere; |Reflux 6.1: sodium hydride / N,N-dimethyl-formamide / 18 h / 20 °C 7.1: hydrogenchloride / water; ethanol / 3 h / -8 °C / |Sealed tube View Scheme

1: 82 percent / aq. NaOH, H2O2 / 4 h / 25 °C 2: K2CO3, cupric oxide / 5.5 h / 110 °C View Scheme